Potassium Iodide → 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 2039680

Reaktionsgleichung

Reaktionsgleichung von HRID 2039680
[OH:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].Cl.Cl[CH2:15][C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[NH2:21][C:18]1[S:19][CH:20]=[C:16]([CH2:15][O:1][N:2]2[C:10](=[O:11])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]2=[O:12])[N:17]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Produkt 1

HCID 3410772-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dioneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-1H-isoindole-1,3(2H)-dione (4.13 g, 15.0 mmol) in acetonitrile (150 mL) were added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (50.1 g, 337 mmol), cesium carbonate (210 g, 643 mmol) and potassium iodide (2.54 g, 15.3 mmol). The heterogenous mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, the insolubles were filtered off, rinsed with water and dried over night to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g, yield 43%; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].

Aufarbeitung

  1. filtrationthe insolubles were filtered off
  2. washrinsed with water
  3. customdried over night

Quellen und Nachweise

ORD-Eintrag
ord-e2ea30608b7442e6bab564d433391754
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580799B2

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